"It's really obvious that I like him, even if he is clueless about this stuff, it's really quite obvious... Plus I'm not 100% sure if he likes me or not, so I don't want to be let down."
Replace every "him" and "he" in this quote with "her" and "she", and this is exactly what is going through his mind.
What makes you say that it's obvious to him that you like him?
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Read that guide I wrote and linked to above.
Understand that there are proactive steps you can take to be less shy to the point of being open to approaching, and being approached in a way that will take the interaction forward.
Read through the entire guide, and let me know if there are any particular areas you need to work on for yourself.
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1Opinion
You make the move. If you can't do it how in the hell are you going to make him?
Girls are so much more picky than guys, so why should they have to ask you?
But in this situation it's ask him or just regret it.
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